GB672936A - Pentaenes and a process for the manufacture thereof - Google Patents

Pentaenes and a process for the manufacture thereof

Info

Publication number
GB672936A
GB672936A GB17026/49A GB1702649A GB672936A GB 672936 A GB672936 A GB 672936A GB 17026/49 A GB17026/49 A GB 17026/49A GB 1702649 A GB1702649 A GB 1702649A GB 672936 A GB672936 A GB 672936A
Authority
GB
United Kingdom
Prior art keywords
acetal
hydroxy
yne
methyl
pentaenes
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB17026/49A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Priority to GB17026/49A priority Critical patent/GB672936A/en
Publication of GB672936A publication Critical patent/GB672936A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/06—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms
    • C07C403/10—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms by etherified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Pentaenes are obtained by condensing an acetal of 1-hydroxy-3-methyl-pentene-(2)-yne-(4), by means of a Grignard reaction, with 4-(21,6161 - trimethyl - cyclohexene - (11) - yl) - 2 - methyl-butene-(2)-al-(1) and subjecting the acetal of 1-hydroxy-3,7-dimethyl-6-hydroxy-9-(21,61,61 - trimethyl - cyclohexene - (11) - yl) - nonadiene-(2,7)-yne-(4) obtained, in any desired sequence, to partial hydrogenation of the triple bond by the addition of one mol. of hydrogen, and to allyl re-arrangement and dehydration. Either the aldehyde-acetal or the keto-acetal of 1 - hydroxy - 3 - methyl - pentene - (2) - yne - (4) may be used for the condensation. In addition a masked acetal may be used, for example, the tetrahydropyranyl ether of 1-hydroxy-3-methylpentene-(2)-yne-(4). Detailed examples are given.
GB17026/49A 1949-06-27 1949-06-27 Pentaenes and a process for the manufacture thereof Expired GB672936A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB17026/49A GB672936A (en) 1949-06-27 1949-06-27 Pentaenes and a process for the manufacture thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB17026/49A GB672936A (en) 1949-06-27 1949-06-27 Pentaenes and a process for the manufacture thereof

Publications (1)

Publication Number Publication Date
GB672936A true GB672936A (en) 1952-05-28

Family

ID=10087872

Family Applications (1)

Application Number Title Priority Date Filing Date
GB17026/49A Expired GB672936A (en) 1949-06-27 1949-06-27 Pentaenes and a process for the manufacture thereof

Country Status (1)

Country Link
GB (1) GB672936A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2676988A (en) * 1951-09-11 1954-04-27 Eastman Kodak Co Method of making vitamin a and intermediates formed thereby
CN115348960A (en) * 2020-03-31 2022-11-15 帝斯曼知识产权资产管理有限公司 Process for the preparation of vitamin A

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2676988A (en) * 1951-09-11 1954-04-27 Eastman Kodak Co Method of making vitamin a and intermediates formed thereby
CN115348960A (en) * 2020-03-31 2022-11-15 帝斯曼知识产权资产管理有限公司 Process for the preparation of vitamin A

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